Acetic Acid → 1'-({6-Chloro-1-[(1-methylpyrrolidin-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 2055540Notes

Reaction equation

HRID 2055540 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]([N:19]3[CH2:24][CH2:23][C:22]4([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[CH2:26][O:25]4)[CH2:21][CH2:20]3)=[O:18])=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:33]C(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]([N:19]3[CH2:24][CH2:23][C:22]4([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[CH2:26][O:25]4)[CH2:21][CH2:20]3)=[O:18])=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][N:14]([CH3:33])[CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 59657701HCID 59657701, compound

Product 1

HCID 596575131'-({6-Chloro-1-[(1-methylpyrrolidin-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1′-{[6-chloro-1-(pyrrolidin-3-ylmethyl)-1H-indol-3-yl]carbonyl}-3H-spiro[2-benzofuran-1,4′-piperidine] in MeOH was treated with aq. H2CO (1.5 eq), AcOH (1.1 eq) and stirred for 15 min at room temperature, then treated with NaCNBH3 (1.1 eq) and stirred at room temperature for 1 h. Concentration and purification by preparative HPLC gave the desired product. ES-MS m/e (%): 464.2(M+H+).

Workup

  1. stirringstirred at room temperature for 1 h
  2. concentrationConcentration and purification by preparative HPLC

Sources & evidence

ORD record
ord-f8f15325dd964f6380afba9c64e44c1b
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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